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[ CAS No. 5637-42-3 ] {[proInfo.proName]}

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Chemical Structure| 5637-42-3
Chemical Structure| 5637-42-3
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Product Details of [ 5637-42-3 ]

CAS No. :5637-42-3 MDL No. :MFCD16251323
Formula : C8H8N4 Boiling Point : -
Linear Structure Formula :- InChI Key :BTDGLZSKNFJBER-UHFFFAOYSA-N
M.W : 160.18 Pubchem ID :17747914
Synonyms :

Safety of [ 5637-42-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5637-42-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 5637-42-3 ]

[ 5637-42-3 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 5637-42-3 ]
  • [ 87-13-8 ]
  • 4-[(1,4-dihydro-4-oxo-2-pyrimidinyl)amino]benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.9% Example 2A mixture of 64 g (0.4 mol) of <strong>[5637-42-3](4-cyanophenyl)guanidine</strong>, 98.4 g (1.2 mol) sodium acetate and 76.6g (0.44 mol) diethyl(ethoxymethylene)malonate in 600 ml N-methylpyrrolidinone (NMP) was heated to 100C and stirred for 1 hour at that temperature. 81 ml of demineralized water was added and the reaction mixture was further heated to reflux temperature. About 120 ml of the solvent was evaporated until the temperature of the reaction mixture reached the range of 155C to 160C. Subsequently the reaction mixture was refluxed during 72 hours. The whole is allowed to cool to 20-25C and 25g filtration aid was added. After stirring the mixture for 1 hour at 20-25C, the precipitate was filtered off and washed with 50 ml of NMP. The solvent was distilled off under vacuum and the residue was heated to 130C. 375 ml acetic acid was added dropwise (during 15 minutes) to the heated residue while keeping the temperature at 130C. After addition of the acetic acid, the mixture was heated to 150C and stirred at EPO <DP n="11"/>that temperature for 15 minutes. Subsequently, the mixture was allowed to cool to 20-25C. The formed precipitate was filtered off and washed with ethanol (1 x 250 ml and 1 x 100ml). 500ml ethanol was added to the washed precipitate and this mixture was heated and refluxed for 1 hour. After cooling to 20-25C, the precipitate was filtered off, washed with 100 ml ethanol and dried at 50C under vacuum during 16 hours. Yield : 80.5g of4-[(l,4-dihydro-4-oxo-2-pyrimidinyl)amino]benzonitrile (75.9 % yield).
  • 2
  • [ 5637-42-3 ]
  • [ 22398-14-7 ]
  • 4-[(1,4-dihydro-4-oxo-2-pyrimidinyl)amino]benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Examples Example 1A mixture of 64 g (0.4 mol) of <strong>[5637-42-3](4-cyanophenyl)guanidine</strong>, 98.4 g (1.2 mol) sodium acetate and 76.6g (0.44 mol) dimethyl(methoxymethylene)malonate in 600 ml N-methylpyrrolidinone (NMP) was heated to 100C and stirred for 1 hour at that temperature. 64.8 ml of demineralized water was added and the reaction mixture was further heated to reflux temperature. About 100 ml of the solvent was evaporated until the temperature of the reaction mixture reached the range of 155C to 160C. Subsequently the reaction mixture was refluxed during 30 hours. The whole is allowed to cool to 20-25C and 25g filtration aid was added. After stirring the mixture for 1 hour at 20-25C, the precipitate was filtered off and washed with 40 ml of NMP. The solvent was distilled off under vacuum and the residue was heated to 120C. 300 ml acetic acid was added dropwise (during 15 minutes) to the heated residue while keeping the temperature at 130C. After addition of the acetic acid, the mixture was heated to 150C and stirred at that temperature for 15 minutes. Subsequently, the mixture was allowed to cool to 20-25C. The formed precipitate was filtered off and washed with ethanol (I x 200 ml and 1 x 80ml). 400ml ethanol was added to the washed precipitate and this mixture was heated and refluxed for 1 hour. After cooling to 20-25C, the precipitate was filtered off, washed with 100 ml ethanol and dried at 50C under vacuum during 16 hours. Yield : 65.6g of 4-[(l,4-dihydro-4-oxo-2-pyrimidinyl)- amino]benzonitrile.
  • 3
  • [ 1093294-35-9 ]
  • [ 5637-42-3 ]
  • 4-[(4-pyrazolo[1,5-b]pyridazin-3-yl-2-pyrimidinyl)amino]benzonitrile [ No CAS ]
  • 4
  • [ 1212390-24-3 ]
  • [ 5637-42-3 ]
  • [ 1212390-27-6 ]
  • 5
  • [ 420-04-2 ]
  • [ 873-74-5 ]
  • [ 5637-42-3 ]
YieldReaction ConditionsOperation in experiment
A solution of P-aminobenzonitrile (100 gm), ethanol (500 ml), concentrated nitric acid (36 ml) and aqueous cyanamide (50%, 54 ml) was heated at reflux. The solution was maintained for 16 hours at reflux. The reaction mass was further cooled to 0C and then added methyl tert-butyl ether (500 ml) at 0 to 5C. The reaction mass was maintained for 5 hours at 0 to 5C and separated solid obtained was collected by filtration to obtain 59 gm of guanidine nitrate.Guanidine nitrate (59 gm) was dissolved in water (590 ml) and then added sodium hydroxide solution (1M, 325 ml). The separated solid obtained was filtered and dried to obtain 33 gm of l-(4-cyanophenyl)guanidine.
33 g A solution of P-aminobenzonitrile (100 gm), ethanol (500 ml), concentrated nitric acid (36 ml) and aqueous cyanamide (50%, 54 ml) was heated at reflux. The solution was maintained for 16 hours at reflux. The reaction mass was further cooled to 0 C. and then added methyl tert-butyl ether (500 ml) at 0 to 5 C. The reaction mass was maintained for 5 hours at 0 to 5 C. and separated solid obtained was collected by filtration to obtain 59 gm of guanidine nitrate. Guanidine nitrate (59 gm) was dissolved in water (590 ml) and then added sodium hydroxide solution (1M, 325 ml). The separated solid obtained was filtered and dried to obtain 33 gm of 1-(4-cyanophenyl)guanidine.
30 g With nitric acid; In methanol; water; at 10 - 65℃; for 8h; 100 g of 4-aminobenzonitrile was dissolved in 500 mL of methanol and cooled the reaction mixture to 10-15 C. 161 mL of con. Nitric acid was added to the reaction mixture followed by 65.6 ml of 50% aqueous solution cynamide to the reaction mixture and maintained the reaction at 65 C. for 8 hrs. Cooled the reaction mass to 0 C. and charged 500 ml of methyl-t-butyl ether at 0 C. The solids were filtered, washed with water and acetone and dried to give 30 g of the product as a solid.
  • 6
  • [ 5637-42-3 ]
  • [ 105-53-3 ]
  • [ 374067-80-8 ]
YieldReaction ConditionsOperation in experiment
With ethanol; sodium; for 12h;Reflux; Diethyl malonate (30 gm) was added to l-<strong>[5637-42-3](4-cyanophenyl)guanidine</strong> (30 gm) at room temperature. A solution of sodium (17.2 gm) in ethanol (450 ml) was added to the above reaction mass. The contents were heated to reflux and maintained for 12 hours. Distilled off the solvent completely under vacuum and then added water (500 ml). The reaction mass was stirred for 30 minutes and filtered. The solid obtained was dried to obtain 40 gm of 4-(4,6-dihydroxypyrimidine-2-yl-amino)benzonitrile.
40g With ethanol; sodium; for 12h;Reflux; Diethyl malonate (30 gm) was added to <strong>[5637-42-3]1-<strong>[5637-42-3](4-cyanophenyl)guanidine</strong></strong> (30 gm) at room temperature. A solution of sodium (17.2 gm) in ethanol (450 ml) was added to the above reaction mass. The contents were heated to reflux and maintained for 12 hours. Distilled off the solvent completely under vacuum and then added water (500 ml). The reaction mass was stirred for 30 minutes and filtered. The solid obtained was dried to obtain 40 gm of 4-(4,6-dihydroxypyrimidine-2-yl-amino)benzonitrile.
6.5 g With methanol; sodium; In methanol; for 6h;Reflux; Inert atmosphere; 5.7 g of sodium metal was added to 200 mL of methanol at 0-5 C. with constant stirring under nitrogen atmosphere. 10 g of compound II dissolved in 200 mL of methanol was added to the solution followed by the dropwise addition of 10 g of diethyl malonate. The reaction mixture was heated to reflux for 6 h. After completion of the reaction, the solvent was removed under vacuum; water was added to the crude mixture and stirred for 30 minutes. The solid was filtered and adjusted the pH of the filtrate to 4.0-6.0. The separated solid was filtered, washed with acetone and dried to give 6.5 g of a solid.
  • 9
  • [ 5637-42-3 ]
  • 4-{6-amino-2-[(4-cyanophenyl)amino]pyrimidin-4-yloxy}-3,5-dimethylbenzenecarbonitrile [ No CAS ]
  • 10
  • [ 5637-42-3 ]
  • [ 1070377-34-2 ]
  • 11
  • [ 1355249-18-1 ]
  • [ 5637-42-3 ]
  • 4-((5'-oxo-6',8'-dihydro-5'H-spiro[cyclopropane-1,7'-quinazolin]-2'-yl)amino)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% In ethanol; for 30h;Reflux; Example 364-((5'-Oxo-6',8'-dihydro-5'H-spiro[cyclopropane-1,7'-quinazolin]-2'- yl)amino)benzonitrile[00178]Spiro[2.5]octane-5,7-dione (390 mg, 2.82 mmol) is dissolved in EtOAc (20 mL), and DMF-DMA (503 mg, 4.22 mmol) is added. The mixture is refluxed for 12 h, then evaporated to dryness to give an intermediate enamine. 165 mg (1 .1 mmol) of this intermediate together with 1 -<strong>[5637-42-3](4-cyanophenyl)guanidine</strong> (175 mg, 1 .1 mmol) are dissolved in abs. EtOH (8.5 ml_). The mixture is heated at reflux for 30 h, then cooled. The formed precipitate is filtered, washed with DEE and dried to provide the title compound (72 mg, 26%).1H NMR (CDCIs), deltaEta, 0.55 (s, 4H), 2.52 (s, 2H), 2.86 (s, 2H), 7.63 (d, 2H), 7.85 (d, 2H), 7.93 (s, 1 H), 9.04 (s, 1 H).LC/MS (M+H)+ = 291
  • 12
  • [ 5815-08-7 ]
  • [ 66116-81-2 ]
  • [ 5637-42-3 ]
  • [ 1383716-96-8 ]
YieldReaction ConditionsOperation in experiment
Preparation of intermediate 4-(4-(2-(methylthio)-6-oxo-l,6-dihydropyrimidin-5- yl)pyrimidin-2-ylamino)benzonitrile (34) : (34)5-Acetyl-2-(methylthio)pyrimidin-4(3H)-one (33) (1.094 g, 5.94 mmol) was dissolved in l-tert-butoxy-N,N,N',N'-tetramethylmethanediamine (12.26 mL, 59.4 mmol), then the reaction mixture was heated at 120C for 6 hours. The reaction mixture was concentrated in vacuo, and dried over high vacuum for 1 hour. The crude intermediate was taken up in DMF (31.6 mL), then l-<strong>[5637-42-3](4-cyanophenyl)guanidine</strong> (2.076 g, 8.91 mmol) and K2C03 (4.10 g, 29.7 mmol) were added. The reaction mixture was heated at 120C for 48 hours. Additional 1 -<strong>[5637-42-3](4-cyanophenyl)guanidine</strong> (2.076 g, 8.91 mmol) and K2C03 (3.69 g, 26.7 mmol) were added, and the reaction mixture was stirred at 120C for additional 18 hours. The reaction mixture was cooled to rt, then was slowly poured into an ice-cooled IN HCl solution while stirring vigorously. The reaction mixture was neutralized with additional IN HCl, then the reaction mixture was allowed to stir for an additional 30 minutes. The resulting precipitate was filtered, washed multiple times with DI water, 2-propanol, then diethyl ether. The resulting crude product was dried over high vacuum for 18 hours to obtain the desired product as a red/brown solid (940 mg, 47% yield). MS (ES+): m/z = 337.2 (100) [MH+]. HPLC: tR = 1.35 minutes over 3 minutes. Purity: 72% [HPLC (LC/MS) at 220 nm].
  • 13
  • [ 5637-42-3 ]
  • [ 105-56-6 ]
  • [ 1398507-07-7 ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; In butan-1-ol; at 60 - 93℃; for 4h; Example 1:Preparation of 4-(4-Amino-6-hydroxypyrimidin-2-ylamino)benzonitr-le (II):2000 ml of n-butanol and 192.8 g of potassium-tert-butoxide were added to the reaction vessel at 45 +/- 5 C and stirred for 30 mins. To the reaction mixture was added 194.42 g of ethylcyano acetate over 15 min and added 250 mL of n-butanol. The reaction mixture was heated to 60 +/- 5 C under stirring and was added 250 g of <strong>[5637-42-3]N-cyanophenyl guanidine</strong> followed by 250 mL of n-butanol and further heated to 93 +/- 3 C, maintained the same at4 hrs with stirring. After completion of the reaction, reaction mixture was cooled to 75 +/-5 C and was added 1750 mL of water and stirred at same temperature for 30 mins. Further, to the reaction mass was added 250 mL of glacial acetic acid; stirred and cooled to Room temperature (RT). The resulting solid was filtered and washed with 500 mL of water followed by washing with methanol and dried to yield titled compound.Dry weight: 290- 330 gm.
330 g With potassium tert-butylate; In butan-1-ol; at 45 - 93℃; for 4h; Example 1 Preparation of 4-(4-amino-6-hydroxypyrimidin-2-ylamino)benzonitrile (II) 2000 ml of n-butanol and 192.8 g of potassium-tert-butoxide were added to the reaction vessel at 45+-5 C. and stirred for 30 mins. To the reaction mixture was added 194.42 g of ethylcyano acetate over 15 min and added 250 ml of n-butanol. The reaction mixture was heated to 60+-5 C. under stirring and 250 g of <strong>[5637-42-3]N-cyanophenyl guanidine</strong> was added, followed by 250 ml of n-butanol and further heated to 93+-3 C., maintained the same at 4 hrs with stirring. After completion of the reaction, the reaction mixture was cooled to 75+-5 C. and 1750 ml of water was added and stirred at the same temperature for 30 mins. Further to the reaction mass was added 250 ml of glacial acetic acid; stirred and cooled to room temperature (RT). The resulting solid was filtered and washed with 500 ml of water, followed by washing with methanol and drying to yield the titled compound. Dry weight: 290-330 gm.
  • 14
  • [ 5637-42-3 ]
  • [ 1398507-08-8 ]
  • 15
  • [ 5637-42-3 ]
  • [ 1404118-66-6 ]
  • 16
  • [ 5637-42-3 ]
  • [ 1404118-67-7 ]
  • 17
  • [ 5637-42-3 ]
  • [ 1404118-68-8 ]
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